50 questions

Part 0: How you operate

  1. What are your strengths and superpowers (beyond functional expertise)?


  • Structured thinking and writing - I think by writing. See what I’m exploring or previously explored
  • Organized and proactive - I keep tabs on a wide range of things to keep everything moving
  • Persistence - I continue working on something until it’s done. Played Go (strategy board game) for a decade until I played on the international stage.


  • Ability to focus and say no - I haven’t watched TV, movies, or played video games for 17 years now.
  • Incentive design and thinking through complex systems - I built a complex odds and LP system at Megapot by asking “how can we make lotteries fair? how can we build big jackpots consistently?”

2. What are your weaknesses? How do you try to compensate for them?

Weaknesses: Can spend too much time thinking, discussing, or overanalyzing.

Compensate: I schedule weekly retros and have weekly goals. I force myself to do things, share ideas, and schedule meetings, even when I’m not fully ready. When I notice myself avoiding or postponing something, I do that first.

3. What words would your co-workers use to describe you? What would they want me to know about what it’s like to work with you?

Themes directly taken from my most recent peer feedback:

  • Good: Tackling complex problems, Action oriented, Kind & Positive, Execution
  • Improve: Overly discussing and consensus reaching, written communication style in a company that is more live discussions, too detailed

4. How do you deal with conflict? Describe a time you dealt with it well — and a time you didn’t.

I like talking directly about it and I use writing to clarify things.

Well - I just joined the backend team. Backend team was always fighting fires with unreliable data providers and dealing with urgent requests from other teams, which meant our priorities were always in disarray. Other teams didn’t like how we could give them fixed timelines or add more documentation. I met with folks, put down priorities in writing, and showed them the stack ranking. Everyone understood the priorities, knew who to contact when they had new features to ask for. We got headcount to double the eng team and moved to an all-in-one data provider.

Not well - Worked with a new designer who focused more on aesthetics than user needs. In a 1:1 design review, I asked probing questions until it was obvious it didn’t meet the goals. I could have said it in a better way, but I told her she needed to understand our users better, and sent her a bunch of UXR decks and research. She later told me that was rude, and wanted me to just tell her what I wanted designed. I had a follow-up conversation to tell her that I try not to be prescriptive when working with design to not constrain creativity, which didn’t end up well either. I ended up asking PMs who worked with her, and we all had similar experiences. We recognized that she was just overwhelmed. Ended up talking to her manager, who reduced her workload.

5. What’s the worst interpersonal conflict you’ve dealt with? How did you handle it?

I was working with a director of engineering and we had very different communication styles. He preferred doing the right thing without regard to feelings or interpersonal dynamics. I cared that I had strong relationships with others.

We found out that the data provider that we were working with was shutting down. He didn’t want to tell other teams, thinking it’d cause people to panic. I believed it was more important for us to share now so teams could make changes gracefully. He didn’t want the news to leak, though later, I told him engineers on other teams had heard about it since it’s a small industry. He was still adamantly a no, and I was planning to leave, so didn’t push back more.

Then, an eng manager reached out to our CEO, the CEO told me to share the news. I wanted to find time with each EM to let them know individually so I could answer questions. The Dir wanted me to announce immediately over Slack, and to give an artificially short deadline so we had buffer time. I did so.

I was the messenger, everyone got mad at how this was done (going from no news to migration must finish in 2 weeks, this is a P0), and I got a lot of flak for it.

I learned what I needed to do better when working with “brilliant jerks” - get ahead of problems, be much more in tune with what is going on, be more proactive, take his thoughts, share it out. Flag issues earlier.

6. How do you cope with stress? Depression? Are there any red flags I can help watch out for?

Stress - Not great. I generally just close myself off and work harder. I recognize this, and try to just share with more people. Leaning on others. Stress relief is hanging out with family.

Depression - Family is my buffer. I think I’m resilient, and generally very positive

Red flags - Like having recommendations before I share, but sometimes I’ll hole myself off for longer than needed - get me to share early

7. How do you arrive at your convictions? What are some key mental models you use to be creative, solve problems, or make decisions?

Conviction - post market evaluation and uxr; Trust my gut, follow my passions, life is an adventure

Creative - just write early and often, will often continue iterating.

Solve problems - break down into disagreements, tackle one by one

Decisions - write down pro’s and con’s

8. Describe your work style. What techniques do you use for personal productivity?

GTD system - I like planning out my day minimally. I have systems in place to check in on important projects and ensure I’m working on what’s most important.

Communication - I like async prep so we’ve all had time to think things through. I like short Slack huddles when needed.

Productivity - I care about my body and environment. This means eating and sleeping well, and being somewhere with sunlight. I batch meetings together in the afternoon to ensure I have long stretches where I’m in the flow.

9. How many hours/week are you willing to work? For how long? What sounds good? What sounds like hell?Do you have different expectations for different phases of the company’s lifespan? (i.e. willing to work harder in the beginning)

I can do 50-55 hours/week and won’t be able to do much on evenings or weekends. I often work late nights or early mornings when I’m excited or if I’m blocking someone.

Can stretch on a few evenings or weekends, but not much since I’m proud to be a family man with a 2 year old daughter.

I’ve found that I can do an allnighter or limited sleep for 1-2 nights, but my best work is done when I get enough sleep regularly.

If there’s too much to do, I prefer to cut scope, cancel meetings, skip events, etc. but care about staying rested. When I’m overwhelmed, I frequently cancel all my meetings for a week to get back on track.

For the first two years, I expect to work 60 hour weeks by focusing exclusively on this and my family, to the exclusion of everything else. I’ve already cut out hobbies, a lot of exercise, and all evening activities.

Hell is inflexibility to adjust scope, meetings that could be shorter/message, feeling like something is a waste of time

Part I. Roles

  1. What would you want your role to be before we reach product/market fit? What would you want your role to be after we reach product/market fit?

Pre-PMF - whatever it takes to find PMF or keep things moving: Coding, design, user interviews, sales, marketing, growth, support.

PMF - scale: Focus on what’s most important for company. Focus on one or two things primarily and do them really well - whether that’s growth, sales, product, etc.

CEO/CPO/COO is fine. Depending on who has a stronger vision and understanding of the problem at hand, that person can be CEO.

11. How do you see your role changing as the company starts toscale? (Read the Review article on giving away your Legos.)

Scale: Less design, growth, sales

I want to still focus on product. I’ve been early product hire at two startups - the first one I didn’t truly understand the product the way the founder did - who spent 4 years building it. The second, I think I did great, but still think the company would have been more effective if the founder should have just delegated other non-product stuff.

12. If your role becomes unavailable entirely (e.g. the board hires a professional CEO or an experienced executive), what would you want your new role to be?

CPO. But not as interested being a middle-level manager. Happy to be an IC PM otherwise. I like building things that users get to use.

13. Areas of Responsibility (AoR) Exercise. Rank yourself in these areas (both as an individual contributor, and as a leader) on a scale of 1-10. Then rate your passion in each of the above areas on a scale of none to high. (e.g. “I’m an 8 in sales, but hate it so none”):

P Strat

Part II. Corporate Structure and Funding

14. Where should our startup be based? How do you feel about remote or distributed teams?

SF in person all week initially. Strong believer in working in the same space. Hybrid OK as we scale.

Since we’ll spend more time at work than we will with anything else, want to be friends with cofounder.

15. Is there anything I should know that may affect materially affect your time or legal status as a founder? (e.g. visa, green card, criminal record)

No - just getting green card from marriage.

16. How should founder equity be set? What’s your philosophy on the employee equity pool?

50-50. more equity for founding employees

17. What should our approach to employee compensation be, including cash and equity?

Personally, want to be scrappy. Pay what everyone needs. Want to take as many shots on goal. Let them adjust cash vs. equity.

I’d rather have a small part of a large pie, than a large part of small pie. Want to work with people for many years, so very much incentive-alignment.

18. How much money should we raise? (i.e. “zero” to “as much as we can”) In the range of “bootstrapped small business” to “go big or go home”, where do you want this startup to go?

VC-backed but grow sustainably. Keep low burn - low salaries, less people, even if that means we handle something of each

Either moonshot product that I believe in significantly, or something that generates money immediately

19. What matters most in a funder? If you were doing reference checks on a VC or potential board member, what traits would you be looking for?

Proactive support - can be super busy, need someone who is thinking about us.

Through the ups and downs - this is a very long-term relationship

Has our best interest in mind - whether it’s this company or the next, believes in us

Brand name helps for recruiting

20. What does an ideal company exit look like to you? (i.e. “work on company for 1-2 years and sell for 7 figures” to “work for 10 + years, reach 9 figures in revenue, and IPO”)

Work for 10+ years, reach significant revenue, IPO

I’m open to sell as well, believe that removing financial pressure allows for a stronger chance of 2nd time founder success

21. How do you think about the timeframe and pace of success? Are you willing to take the longer path? How long is too long?

Giving myself 2 years to build conviction and get to break even expenses ($100k/year)

I think I’d check in every year - if I’m still learning, down to continue.

Prefer things that I can validate hypotheses in ≤1 month 22. What number would you sell at? How would that change if you got extra liquidity from your existing positions?

Depends on how much time and effort we’ve put in. After a few years, I think $5M+ post-tax for me individually. It’s an amount that means we can take as many shots on goal in the future with no pressure.

If I got liquidity to buy a house ($1.5M post-tax), then bar would be very high (8 figures+).

23. What do we do if we find product/market fit, yet none of the founders are excited about that product?

Happy to have someone else work on it. I want to be excited about what I work on, that’s why I’m founding.

24. Can one co-founder fire another co-founder? Can someone else fire a founder?

Yes. But that’s a failure on our part. Upfront communication, set expectations. But ultimately do what’s best for company

Part III. Personal Motivation

25. Why do you want to start a company — in general, and in particular right now?

I want to work on ideas that I can’t stop thinking about. Also, lets me build the culture/work environment I want. Right now - because there isn’t a better time, and because I’m obsessed.

26. What is success to you? What motivates you personally?

Success is working on what I enjoy, with people I enjoy, and how I do it.

Financially, ROI tapers off quickly. After having a paid off house with no financial pressure, the things above matter most.

Personal - I like what I’m working on. I like our progress, which means coming up with hypotheses and validating/invalidating them quickly.

27. What impact do you want to have? Is your startup objective “getting rich” or “changing the world”? Is control or success more important? (i.e. Are you willing to step aside if the company is more likely to have a financially successful outcome or is it important for the founders to stay in control of the company’s destiny?)

Impact on the world, make the world better, changing the world

Success more important, will step aside if I’m not the right person.

28. What makes you gritty?

Discipline - habits

Focus - willing to say no to almost everything to work on one thing

Personal motivation - making a dent in the universe, my time to give this my best shot

29. Who do you admire most in your organization/family/friends and why?

People who’ve listened to their hearts and taken the plunge

Those who are able to be present with friends and family

30. What are you most proud of in your work career or life to date?


  • Listened to my gut. Left Microsoft for a startup (Teespring), left Microsoft again for another startup (Kite), then left Lyft for a third startup (Genie).
  • Proud of the NFT marketplace we shipped at Uniswap/Genie - every interaction and UI was sublime. At Lyft, launching Priority Mode, which was a complex data science, eng, and design effort. Scaling it to a bunch of cities which took judgement calls and working with ops. Gas surcharge at Lyft - busiest 2 weeks of my life, but we responded to changing market conditions quickly.

Life - listened to my heart, taking leaps of faith. proposed when I was 25, got married at 26, had a baby at 28.

31. When have you taken a chance when others did not? Or when have you been willing to take an unpopular stance?

Taken a chance

  • Leaving home to go to a school in a different country (Canada → UNC)
  • Jumping for startups
  • Marriage at a young age


  • Doubling down on crypto. Just following my heart.
  • In social situations, always reaching out to those who are left out. I’ve been there before.

32. What are some of the products and companies you love, and why?

Uniswap - i have always wanted to build things that are good for the public. Love how you can do that and be financially valuable

Blur/Blast - love how they designed the incentives to win market share

Apple - love well-designed hardware

Notion - maximally customizable to meet your needs

33. Is it possible to build a wildly successful company without burning out or damaging other parts of your life (family, health, etc.)?

Yes. But I think it takes discipline. I think it’s a forcing function to only work on what’s important, and to say no to a lot more, take your time before shooting your shot.

Part IV. Commitment and Finances

34. Will this company be your primary activity? Do you have any other time commitments?

Yes. Daughter.

35. What is your expected time commitment right now? How do you see that changing in the next 6 months? 2 years?


May change if we have another kid, which I hope to but is unlikely. I’ll likely see hours reduce to 40/week for 3 months.

36. What is your personal runway? Current burn rate? Would you invest your own money (ideally retaining higher equity in return)?

Personal runway, $100k for 2 years. Low burn, ~4k/month. As mentioned earlier, as long as I hit break-even ($50k/yr takehome) I’ll be fine to continue, as long as I’m interested in what I’m working on, learning how to build a business, and believe this can be big.

To a limit, probably another $50k. Though preference to raise a round if we have some traction. At that point, seems like a better tradeoff to reduce risk.

37. What is the minimum monthly salary you need to survive? To be comfortable? To feel like you’ve “made it?”

Takehome amounts -

  • Min: $50k/year, to cover expenses, no mortgage
  • Comfortable: $150k/year, can pay off a condo mortgage together with wife’s income
  • Made it: Probably $1M/year. I can make $400k at bigtech, so it’d have to be meaningfully higher

38. What should the policy of co-founders advising/consulting with other companies be?

Trust other cofounders. I think if it’s limited (1-2h/week), sure.

If it’s paid consulting to pay the bills, we should discuss finances. Happy to do whatever’s necessary (eg. raise a round sooner) to ensure we can give 100% focus.

Personally, I won’t, since I know that the mental overhead isn’t worth it for me.

Part V. Team Culture

39. Complete the sentence: It would make you proud to hear people describe this company’s culture as _________________. (Values are written words, and your culture is how you actually live those written words.)

Ambitious, owner mentality, proactive, caring, focused

40. What’s your philosophy on how to attract and retain great people? Tactically, how would we make this happen at our company?

Give them space to do what they want to do best, and meaningful work.

This doesn’t mean laissez faire, it means thinking really hard about setting the right lanes for them. It means making sure that this is a long-term need, which means doing it for a bit too long ourselves until we know it’s needed.

41. What processes or techniques would you use to get the most out of your team? For example, how would you help them become better managers or achieve their goals?

Constant and direct feedback.

Understand their goals and how we can meet them.

Align on goals, not processes. Trust others to be high performers and figure it out.

Don’t let them burn out:


42. How much of your time do you hope to spend either working or socializing with coworkers?

Working - 50/hr week

Socializing - 3-5/hr, includes lunch

One saying I believe is “You spend more time at work than with your family, so make sure you enjoy where you work.” Doesn’t mean we need to go out all the time, but I want to enjoy lunchtime and get along with people.

43. How important is diversity & inclusion? Concretely, how would you put that into action?

Somewhat important. I care much more about inclusion, and will try my best at recruiting diversity

I’ve liked environments like Lyft, Uniswap where it’s a friendly environment with diverse perspectives.

Make it easy for people to share thoughts/agendas without feeling like they’re risking something, having to jump in in meetings, need specific credentials

Part VI. Co-Founder Relationship

44. Specifically, how are we going to prioritize and make time for our co-founder relationship as we get increasingly busy with company building?

Scheduled chat weekly to talk about state of relationship

Talk often, regularly, and as needed, every day, about anything

Work in person - best way to read body language, discuss over lunch, etc.

45. How would we resolve personal conflict between ourselves? How about stalemates?

If it needs one day for emotions to calm, sure, but don’t ever let emotions grow over time.

Talk it out, usually it’s a bunch of different problems, approach each problem directly. Be sincere, assume other person has best interest in mind as well.

Understand conviction, be flexible since we trust each other

If something can be tested, go with whatever is fastest to test

Disagree and commit

Bring in outside advice is absolute last

46. In case this becomes part of our partnership’s evolution, how would you go about handling a startup divorce?

Figure out who cares most about going with the existing company.

They need equity that allows them the best chance to succeed, which likely means another cofounder or raising a round, so cap table needs to work. Goal is to build a billion dollar company, and that’s really it

I want to part on good terms, what matters is the startup doing well - eg. like a family, making sure the kids are cared for and happy

Vest what they’ve vested.

Thank them profusely for contributions.

47. What happens in the scenario where we aren’t growing? How would we diagnose the problem? How have each of our capabilities and approach contributed to growth failures in our pasts?

Make hypotheses. Check in regularly. Share updates. Measure a lot.

Strategic & Tactics. If it’s the industry, the role, etc. Also, how we work together.

What I’ve seen in the past:

  • Not truly obsessing over the users’ needs, so we end up building things that aren’t needed. You need to live their experience to understand it.
  • Confront realities. If macro situation or user behavior has changed, respond quickly.

48. In every partnership, there are times when a partner might breed resentment if certain dissatisfactions don’t change over time. How would you deal with a situation like this?

Get to resolutions and closure. Your feelings are your feelings, and you have every right to feel that way. If there isn’t change, bring it up again. Be clear how important it is.

I will do whatever I can to ensure that you feel heard. I will keep track of, and always make sure to fix, anything that matters to you.

49. How would you think about bringing on a third (or N+1) cofounder?

More risky, not a priority.

Would want us to work well first. But strong referral and strong need, open to it.

50. Wrap up question: Now we know each other’s weaknesses, passions, needs and constraints––how are we going to make each other successful? What would it take to feel truly partnered in this adventure?

Be extremely open and candid all the time. Have honest conversations.

Always talk about our thoughts on various time scales - daily, weekly, monthly, yearly. Understand how we’re feeling at all times, and how we feel about the future, to avoid surprises.